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Mechanochemical Thiocyanation of Aryl Compounds via C-H Functionalization.

ABSTRACT: Aryl thiocyanate compounds are important building blocks for the synthesis of bioactive compounds and intermediates for several functional groups. Reported thiocyanation reactions via C-H functionalization have limited substrate scope and low RME. The ball-milling method reported here uses ammonium persulfate and ammonium thiocyanate as reagents and silica as a grinding auxiliary. It afforded aryl thiocyanates with moderate to excellent yields for a wide variety of aryl compounds (36 examples, 8-96% yield), such as anilines, phenols, anisoles, thioanisole, and indole, thus tolerating substrates with sensitive functional groups. New products such as benzo[d][1,3]oxathiol-2-ones were obtained with C-4 substituted phenols. Thus, to our knowledge, we report, for the first time, aryl thiocyanation reaction by ball-milling at room temperature and solvent-free conditions, with short reaction times and no workup. Analysis of several mass-based green metrics indicates that it is an efficient greener method.

SUBMITTER: de Oliveira Lima Filho E

PROVIDER: S-EPMC7774286 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Mechanochemical Thiocyanation of Aryl Compounds <i>via</i> C-H Functionalization.

de Oliveira Lima Filho Edson E Malvestiti Ivani I

ACS omega 20201214 51

Aryl thiocyanate compounds are important building blocks for the synthesis of bioactive compounds and intermediates for several functional groups. Reported thiocyanation reactions <i>via</i> C-H functionalization have limited substrate scope and low RME. The ball-milling method reported here uses ammonium persulfate and ammonium thiocyanate as reagents and silica as a grinding auxiliary. It afforded aryl thiocyanates with moderate to excellent yields for a wide variety of aryl compounds (36 exam ...[more]

PMID: 33403295

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Dataset Information

Mechanochemical Thiocyanation of Aryl Compounds via C-H Functionalization.

Publications

Mechanochemical Thiocyanation of Aryl Compounds <i>via</i> C-H Functionalization.

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